Antiplasmodials from natural resources 2010-2019 | ||||
Degotte G, Pirotte B, Francotte P, Frédérich M. Overview of natural antiplasmodials from the last decade to inspire medicinal chemistry. Curr Med Chem. 2021 Mar 29. PMID: 33781183. pub ahead of print. | ||||
Compound | Antiplasmodial Strains | IC50 (µM) | ||
Antiplasmodial & cytotoxic activities of reported flavonoid structures | ||||
Luteolin 7-O-glucoside | TM4/8.2 | 6.2 ± 2.2 | ||
K1CB1 | 4.5 ± 2.2 | |||
Quercetin 3-O-beta D-glucopyranoside | 3D7 | 5.5 | ||
Dd2 | 4.1 | |||
D6 | 43 ± 0.3 | |||
W2 | 106 ± 1 | |||
Volkensifkvone | F32 | 1.8 ± 1.2 | ||
FcM29 | 1.7 ± 3.7 | |||
Chamaejasmin | Pf | 4.3 | ||
(3E,3'E)-1,1'-(((2S,3R,4R,5S,6S)-2-((5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)-5-hydroxy-6-methyltetrahydro-2H-pyran-3,4-diyl)bis(oxy))bis(4-(4-hydroxyphenyl)but-3-en-2-one) | HB3 | 0.6 ± 0.2 | NA | |
NHP1337 | 7 ± 1 | NA | ||
(3E,3'E)-1,1'-(((2S,3R,4R,5S,6S)-2-((5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)-5-hydroxy-6-methyltetrahydro-2H-pyran-3,4-diyl)bis(oxy))bis(4-(4-hydroxyphenyl)but-3-en-2-one) | HB3 | 2 ± 0.6 | NA | |
NHP1337 | 4 ± 1.0 3 | NA | ||
5,7-dihydroxy-3-(((2S,3R,4R,5S,6S)-5-hydroxy-4-(((E)-4-(4-hydroxyphenyl)-2-oxobut-3-en-1-yl)oxy)-3-(((Z)-4-(4-hydroxyphenyl)-2-oxobut-3-en-1-yl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2-(4-hydroxyphenyl)-4H-chromen-4-one | HB3 | 0.5 ± 0.03 | NA | |
NHP1337 | 4.1 ± 0.5 | NA | ||
(3Z,3'Z)-1,1'-(((2S,3R,4R,5S,6S)-2-((5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)-5-hydroxy-6-methyltetrahydro-2H-pyran-3,4-diyl)bis(oxy))bis(4-(4-hydroxyphenyl)but-3-en-2-one) | HB3 | 1.8 ± 0.4 | NA | |
NHP1337 | 7 ± 1 2 | NA | ||
(2R,3R,4S,5R,6S)-6-((5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-(((E)-4-(4-hydroxyphenyl)-2-oxobut-3-en-1-yl)oxy)-2-((E)-5-(4-hydroxyphenyl)-3-oxopent-4-en-1-yl)-5-methoxytetrahydro-2H-pyran-3-yl acetate | HB3 | 0.6 ± 0.1 | NA | |
NHP1337 | 2.1 ± 0.6 | NA | ||
(2R,3R,4S,5R,6S)-6-((5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-(((E)-4-(4-hydroxyphenyl)-2-oxobut-3-en-1-yl)oxy)-2-((Z)-5-(4-hydroxyphenyl)-3-oxopent-4-en-1-yl)-5-methoxytetrahydro-2H-pyran-3-yl acetate | HB3 | 0.9 ± 0.2 | NA | |
NHP1337 | 5 ± 1 | NA | ||
(2R,3R,4S,5R,6S)-6-((5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-(((Z)-4-(4-hydroxyphenyl)-2-oxobut-3-en-1-yl)oxy)-2-((((E)-4-(4-hydroxyphenyl)-2-oxobut-3-en-1-yl)oxy)methyl)-5-methoxytetrahydro-2H-pyran-3-yl acetate | HB3 | 0.8 ± 0.1 | NA | |
(2R,3R,4S,5R,6S)-6-((5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-(((E)-4-(4-hydroxyphenyl)-2-oxobut-3-en-1-yl)oxy)-2-((((Z)-4-(4-hydroxyphenyl)-2-oxobut-3-en-1-yl)oxy)methyl)-5-methoxytetrahydro-2H-pyran-3-yl acetate | NHP1337 | 4 ± 1 | NA | |
(2R,3R,4S,5R,6S)-6-((5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-(((E)-4-(4-hydroxyphenyl)-2-oxobut-3-en-1-yl)oxy)-2-((((E)-4-(4-hydroxyphenyl)-2-oxobut-3-en-1-yl)oxy)methyl)-5-methoxytetrahydro-2H-pyran-3-yl acetate | HB3 | 2.1 ± 0.9 | NA | |
NHP1337 | 3.8 ± 0.6 | NA | ||
Lonchocarpol | Pf | 4.1 | ||
MS-II | D6 | 4.6 ± 1.1 | ||
3D7 | 1.7 ± 0.1 | |||
KSM009 | 1.5 ± 0.1 | |||
Carphorin B | Dd2 | 3.4 ± 0.4 | ||
Torellianone E | 3D7 | 3.2 ± 0.3 | NA | |
Dauphinol A | Dd2 | 4.7 ± 0.3 | NA | |
Dauphinol B | Dd2 | 0.8 ± 0.1 | NA | |
(2S)-7-O-galloyl-5,3',4-trihydroxyflavan | K1 | 0.6 | ||
Antiplasmodial activities of reported phenolic compounds | ||||
(2S)-7,3-O-digalloyl-5,4'-dihydroxyflavan | K1 | 1.4 | ||
Sigmoidin A | K1 | 3 | ||
Sigmoidin F | K1 | 2.3 | ||
4'-O-methylsigmoidin B | K1 | 2.3 | ||
K1 | 4.4 | |||
K1 | 4.4 | |||
Abyssinin III | K1 | 2.3 | ||
Lophirone E | 3D7 (asex.) | 38.5 ± 3.2 | ||
W2 (asex.) | 12.2 ± 2.1 | |||
3D7 (gam.) | 0.1 ± 0.04 | |||
Alpha'-chlorophirone | 3D7 (asex.) | >50 | NA | |
W2 (asex.) | 17.9 ± 5 42 | |||
3D7 (gam.) | 4.1 ± 1.4 43 |
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Lakoochanoside B | K1 | 2.8 | NA | |
Cycloartocarpin | K1 | 2.7 | ||
5'-prenyl-pratensein | K1 | 2.9 | NA | |
4-{2-rel-(1R,3R,5S)-7-oxo-2,6-dioxabicyclo[3.3.1]non-3-yl]ethyl}phenyl 3,4,5-trihydroxybenzoate | NF54 | 2.4 ± 0.5 | NA | |
Methyl gallate | 3D7 | 4.9 ± 3.3 | ||
3D7 | 1.1 ± 0.2 | |||
Dd2 | 1.6 ± 0.2 | |||
Ethyl gallate | Dd2 | 9.3 ± 3.1 | ||
D6 | 7 | |||
W2 | 4.2 | |||
Lauryl gallate | Dd2 | 2.2 ±0 .2 | ||
2-(6-benzoyl-beta--D-glucopyranosyloxy)-7-(1-alpha, 2-alpha, 6-alpha-trihydroxy-3-oxocyclohex-4-enoyl-5-hydroxybenzyl alcohol | 3D7 | 3.2 ± 0.1 | NA | |
Ellagic acid | W2 | 0.7 ± 0.02 | NA | |
Achyroclinopyrone A | NF54 | 3.8 ± 0.6 | NA | |
Achyroclinopyrone B | NF54 | 1.2 ± 0.01 | NA | |
16Z/E-Achyroclinopyrone D | NF54 | 2.6 ± 0.1 | NA | |
23-methyl-6-O-desmethylaurecepyrone | NF54 | 2.5 ± 0.1 | NA | |
Cladophorol A | Dd2 | 2.7 | ||
Cladophorol B | Dd2 | 4.1 | ||
Acronylin | 3D7 | 1.8 | ||
Spyroaxillarone A | Dd2 | 3.1 | NA | |
K1 | 2.3 | NA | ||
Uvarin B | K1 | 4.8 ± 0.4 | NA | |
Uvarin C | K1 | 4.9 ± 0.3 | NA | |
4-O-geranylisoliquiritigenin | 3D7 | 3.7 | ||
Dd2 | 7 | |||
Moracin C | K1 | 3.5 | ||
Arcotrione | 3D7 | 2.4 | NA | |
Dd2 | 4.7 | NA | ||
Xanthoquinodine A6 | K1 | 0.9 | NA | |
Ketoxnthoquinodine A6 | K1 | 3.7 | NA | |
Xanthoquinodine B4 | K1 | 0.5 | NA | |
Xanthoquinodine B5 | K1 | 0.9 | NA | |
MDN-0185 | 3D7 | 0.009 | ||
Secalonic acid F | K1 | 2.2 | ||
Macluraxanthone | F32 | 1.2 ± 0.3 | ||
FcM29 | 0.9 ± 0.2 | |||
Luteoskyrin | K1 | 0.9 | ||
Knipholone X | 3D7 | 1.93 | ||
HB3 | 4.9 ± 0.6 | |||
NHP1337 | 5 ± 2 | |||
Knipholone anthrone X | 3D7 | 0.7 | ||
Mansonone D | K1 | 2.3 | ||
4'-methylhonokiol | Dd2 | 2.8 ± 0.1 | ||
Magnolol | Dd2 | 3.4 ± 0.1 | ||
Ent-mururin A | K1 | 4.7 ± 2.9 | NA | |
Antiplasmodial activities of reported terpenoid molecules | ||||
Iso-mukaadial acetate | D6 | 4.9 ± 1.9 | ||
W2 | 3.6 ± 0.3 | |||
Trichodermin | NF54 | 1.4 ± 0.3 | ||
6'12'-epoxymyrotoxin A | K1 | 0.1 | NA | |
K1 | 0.002 | NA | ||
7'-hydroymitoxin B | K1 | 0.002 | NA | |
Miotoxin A | K1 | 0.002 | ||
Smenotronic acid | K1 | 0.002 | ||
Ilimaquinone | D6 | 3.9 ± 0.3 | ||
W2 | 2.3 ± 0.3 | |||
Pelorol | Dd2 | 3.5 ± 0.6 | ||
Neoboutomacroin | Dd2 | 2.1 ± 0.2 | ||
Montanin | Dd2 | 0.8 ± 0.2 | ||
Cyathinin A | K1 | 2.1 | ||
Stratin C | K1 | 1.4 | ||
Striatal A | K1 | 1 | ||
Striatal B | K1 | 0.9 | ||
Striatal C | K1 | 2.1 | ||
Ferruginol | NF54 | 2.9 | ||
Leriifoliol | NF54 | 0.4 ± 0.1 | ||
Leriifolione | NF54 | 3.6 ± 0.2 | ||
Antiplasmodial activities of reported triterpenoid structures | ||||
Peyssonnoside A | Dd2 | >6.3 | ||
D10 | >6.3 | |||
3-O-acetyloleuritolic acid | D6 | 15 ± 1.6 | ||
W2 | 4.5 ± 1.1 | |||
(1R,3aS,5aR,5bR,8S,9S,11aR)-3a-(hydroxymethyl)-8-((Z)-5-(4-hydroxyphenyl)-3-methylenepent-4-en-1-yl)-5a,5b,8,11a-tetramethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol | HB3 | 0.9 ± 0.1 | NA | |
NHP1337 | 0.9 ± 0.1 | NA | ||
(1R,3aS,5aR,5bR,8S,9S,11aR)-3a-(hydroxymethyl)-8-((Z)-5-(3-hydroxyphenyl)-3-methylenepent-4-en-1-yl)-5a,5b,8,11a-tetramethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol | HB3 | 0.8 ± 0.4 | NA | |
NHP1337 | 1.5 ± 0.1 | NA | ||
((1R,3aS,5aR,5bR,8R,9S,11aR)-9-hydroxy-5a,5b,8,11a-tetramethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a,8-diyl)dimethanol | HB3 | 3.4 ± 0.5 | NA | |
NHP1337 | 5.2 ± 0.3 | NA | ||
(1R,3aS,5aR,5bR,8R,9S,11aR)-3a,8-bis(hydroxymethyl)-5a,5b,8,11a-tetramethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl (E)-3-(4-hydroxyphenyl)acrylate | HB3 | 1.9 ± 0.2 | NA | |
NHP1337 | 1.4 ± 0.2 | NA | ||
(E)-4-(4-hydroxy-3-methoxyphenyl)-1-(((1R,3aS,5aR,5bR,8R,9S,11aR)-3a-(hydroxymethyl)-9-methoxy-5a,5b,8,11a-tetramethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-8-yl)methoxy)but-3-en-2-one | HB3 | 0.5 ± 0.2 | NA | |
NHP1337 | 0.3 ± 0.03 | |||
Polycarpol | K1 | 3.0± 3.3 | ||
3-O-beta-D-glucopyranoside-sitosterol | 3D7 | 3.2± 0.4 | NA | |
Dd2 | 9.0± 1.7 | NA | ||
3D7 | 32± 3.3 | NA | ||
INDO | >34 | NA | ||
Isoflindissol lactone | NF54 | 2.2 | ||
Eurycomanone | NF54 | 4.2 | ||
Eurycomanol | 3D7 | 0.005 | ||
Isoflindissone lactone | 3D7 | 0.4 | ||
18-dehydro-6- alpha-hydroxyeury comalactone | 3D7 | 0.3 | NA | |
Perovkone C | NF54 | 0.6 | NA | |
Perovkone E | NF54 | 1.3 | NA | |
Perovkone F | NF54 | 3.6 | NA | |
Salvadione D | NF54 | 1.9 | ||
Salvadione A | NF54 | 1.1 | ||
Variecolin | K1 | 4 | ||
3-O-acetyl-7-O-benzoyl ceanotic acid methylester | K1 | 4.6 | NA | |
Halymeniaol | 3D7 | 3 | ||
Ganoderic acid AW1 | D6 | 0.3 | ||
W2 | 2 | |||
Kaimanol | 3D7 | 0.4 | ||
Saringosterol | 3D7 | 0.00025 | ||
Grandifolione | K1 | 1.4 | ||
7-deacetylkhivorine | K1 | 2.5 | ||
Kotschienone A | 3D7 | 2.4± 0.2 | ||
Kotschienone B | INDO | 2.6±0.4 | ||
3D7 | 1.7± 0.3 | NA | ||
INDO | 1.7± 0.3 | NA | ||
7-deacetylgedunin | 3D7 | 4.2± 0.7 | ||
INDO | 5.1± 0.5 | |||
7-deacetyl-7-deoxogedunin | 3D7 | 6.1± 1.1 | NA | |
INDO | 4.5± 1.5 | NA |